Back in 2001, he sold his first company, Firstmark Communications, to PSInet, a big ISP. It was too much after the dot-com boom peaked to make him rich, but it gave him the startup bug.

"Had I sold the business a year earlier, it would have been materially life changing. A year later, it would have been a complete disaster … so it was right in the middle," he said. But "the experience convinced me to do entrepreneur things rest of my life."

A couple years later, in 2003, he had barely launched his second startup when Cisco came along and offered him a deal. It would invest in his startup and the product he built would belong to Cisco. Taking Cisco's deal "took the risk out" and "gave me the opportunity to build a product I wanted to build."

He didn't want to work for others, but he learned a lot from the years he did. "I had never worked in a great, well-run company before," and Cisco was such a place, he says, adding that he still thinks it is.

In 2008, he had the startup itch again, with no idea of what product or service to build. So, he did a six month stint as a entrepreneur in residence with Mohr Davidow Ventures (MDV) where he decided to build a cloud.

MDV handed him a seed check. Then Lehman Brothers, and the whole economy, collapsed.

His new venture would require a lot of capital investment, much like Firstmark. He had no job, a wife, a kid and a second on the way. But he didn't trust that he could make it work.

So he gave the money back and walked away.

All told he says he spent two years "in the wilderness" unemployed and directionless. All he knew was that he wanted to start a new company.

He would soon meet Garg and the two of them would hit it off so well, they would agree to launch BloomReach over a mere three meetings. They would land $5 million in seed money from Bain Capital Ventures with nothing more than the two of them and a PowerPoint presentation, he laughs.

BloomReach is now three years old, has 60 employees and about 70 customers with $16 million in funding.

From all his experience, he was able to create the culture he wants to lead. BloomReach has several founding principles, he says.